Diners and Deals

Welcome to Diners and Deals, the podcast where we dive deep into the journeys of entrepreneurs, business leaders, and investors making big moves in the business world. I’m your host, Seth, and in each episode, we bring you candid conversations with incredible guests who share their insights, successes, and the challenges they’ve faced along the way. Whether it’s scaling a business, navigating private equity, or reinventing an industry, our guests bring a wealth of experience and a fresh perspective to the table. We go beyond the boardroom, discussing the personal stories and pivotal moments that have shaped their careers and the companies they’ve built. Grab a coffee, pull up a chair, and join us as we talk shop in a casual, down-to-earth setting that feels more like catching up with old friends than a traditional business podcast. If you’re passionate about business, growth, and learning from those in the trenches, you’re in the right place. Welcome to Diners and Deals—let’s get into it!

From Chaos to Clarity: Building Enduring Service Businesses - John Barrett - Executive Director at ISSA 06/19/2025

From Chaos to Clarity: Building Enduring Service Businesses - John Barrett - Executive Director at ISSA In this episode of Diners and Deals, host Seth Deutsch sits down with his longtime friend John Barrett to trace the pivotal moments of John’s career—from earning a life-changing Evans Scholarship to learning the ropes at Xerox, turning around broken service businesses, and ultimately leading ISSA, a trade association serving over 11,000 members across 130 countries. John opens up about what really matters in business and life, sharing hard-won wisdom on resilience, humility, and the power of staying curious. They discuss: * Why cash equals time, and how that truth shaped his approach to turnarounds and growth * Lessons in humility and leadership from corporate America and chaotic service businesses * How John scaled Chemco from two states to a 10,000-employee national player * The strategic exit to Compass Group and what he learned from a near-catastrophic customer concentration issue * His reflections on ambition, self-awareness, mentorship, and legacy as he prepares to retire A compelling listen for entrepreneurs, operators, and anyone navigating the messy, meaningful road of business building. Links: John on LinkedIn - ISSA - Seth on LinkedIn - Topics: (00:00:00) - Intro (00:02:57) - John's early life and career beginnings (00:04:21) - Hanukkah memories and personal stories (00:07:02) - John's role at ISSA (00:10:08) - John's upbringing and family life (00:15:14) - College years and early career aspirations (00:20:58) - Journey at Xerox and transition to the service industry (00:38:07) - Mastering cashflow forecasting (00:38:15) - Lessons from recessions and turnarounds (00:39:28) - The brutal reality of layoffs (00:40:25) - The importance of mentorship (00:42:48) - Navigating family-owned businesses (00:45:56) - Scaling and cash management (00:50:11) - Customer concentration risks (00:52:46) - Selling to private equity (01:01:17) - The journey with SMS (01:05:36) - Reflections on leadership and legacy (01:13:11) - Concluding thoughts and farewell /episode/index/show/8b573379-d184-42ce-88fc-90115eccbbeb/id/37044040

From Stuntman to Service Empire: Building with Grit and Purpose - Josh Zolin - CEO of Windy City Equipment 05/15/2025

From Stuntman to Service Empire: Building with Grit and Purpose - Josh Zolin - CEO of Windy City Equipment In this episode of Diners and Deals, I sit down with Josh Zolin, CEO of Windy City Equipment, to talk about what it takes to build a service business that scales—without losing your soul. Josh started his career as a Hollywood stuntman before joining his father’s one-man repair operation. Over time, he helped transform the company into a multi-state commercial kitchen equipment service provider, while staying deeply connected to the skilled trades. We dig into Josh’s journey of self-discovery, from identity struggles and career pivots to a defining personal tragedy that reshaped how he leads. He shares how he built a values-driven company culture, why presence matters more than growth at any cost, and how writing his book Blue Is the New White helped him advocate for the next generation of skilled workers. We also cover: The challenges of scaling high-trust service operations What it takes to expand into new markets—and when to pull back Lessons in leadership, hiring, and letting go of ego How to structure a business that prioritizes people and reputation The evolving conversation around private equity in the trades The emotional and personal growth required to lead with authenticity This episode is a powerful reminder that building a great business starts with understanding who you are—and having the courage to grow alongside it. Links: Josh on LinkedIn - Windy City Equipment - Seth on LinkedIn - CSuite Financial Partners - Topics: (00:00:00) - Intro (00:02:29) - Introducing Josh Zolin (00:05:57) - The Origins of Windy City Equipment (00:07:22) - From Technician to Business Leader (00:21:50) - A Family Tragedy and Transformation (00:31:51) - Expanding the Business and Writing a Book (00:35:00) - Starting a Career in Skilled Trades (00:37:52) - Lessons Learned from Expansion (00:42:33) - Building and Restructuring the Organization (00:51:23) - Navigating Financial Leadership Challenges (00:54:50) - Vision for the Future and Private Equity (01:00:43) - The Importance of Presence and Overcoming Fear (01:06:48) - Closing Remarks and Reflections /episode/index/show/8b573379-d184-42ce-88fc-90115eccbbeb/id/36565380

The Investrepreneur Model: Marrying Vision with Execution - Scott Silverman - Founder and CEO of Agman 04/17/2025

The Investrepreneur Model: Marrying Vision with Execution - Scott Silverman - Founder and CEO of Agman In this episode of Diners & Deals, host Seth Deutsch sits down with Scott Silverman, founder and managing partner of Agman, for an in-depth look at how a multi-generational investment firm is quietly building and backing enduring companies in sectors often overlooked by traditional private equity. Scott shares his unconventional path—from earning a PhD in molecular genetics at Oxford to working at BCG and biotech venture firms, and eventually launching Agman with family capital just before the Great Financial Crisis. What started as a fund of funds has grown into a diversified investment firm with meaningful holdings in real estate, restaurants, insurance, and more. The conversation dives into: Agman's approach to “Investrepreneurship” and backing operators from day zero Building Ampler, a restaurant platform with 500+ units across Taco Bell, Burger King, and more How a cold call led to Vertus, a fast-growing insurance brokerage The creation of Omaha National and AEN Entity, two insurance companies born from within Agman What it takes to move from passive investing to hands-on company building Lessons in partnership, patience, and spotting long-term value Scott also reflects on the emotional realities of entrepreneurship, the power of elegant solutions, and how he balances a high-conviction investing career with life at home. Whether you’re an operator, capital allocator, or founder building in a niche market, this episode offers a rare window into how real value gets created—over time, and with intention. Links: Topics: (00:00:00) - Intro (00:05:51) - Being an Investrepreneur (00:07:06) - Scott’s portfolio companies (00:11:15) - Scott’s upbringing and influences (00:13:26) - The values of being an investor (00:14:59) - Undergrad/Graduate experiences + Early career (00:25:38) - Forming and scaling Agman (00:43:11) - How Agman is geared to help founders (00:46:12) - Building out finance and accounting teams (00:52:50) - Maintaining health and marriage alongside a career (01:01:01) - Closing thoughts /episode/index/show/8b573379-d184-42ce-88fc-90115eccbbeb/id/36197445

Creating Long-Term Value in Niche Markets Through Operational Excellence - Dave Rauch - CEO @ ProTec 03/27/2025

Creating Long-Term Value in Niche Markets Through Operational Excellence - Dave Rauch - CEO @ ProTec In this episode of Diners and Deals, host Seth Deutsch sits down with Dave Rauch, founder and CEO of ProTec, a company that has spent nearly three decades redefining how homeowner associations (HOAs) approach maintenance. With over 370 employees, eight offices, and more than 1,000 communities served across Southern California and Las Vegas, Dave has built a business that fills a major gap in a largely overlooked industry. They dig into the unique operational challenges of serving HOAs, the massive opportunity in preventive maintenance, and how Dave has layered on services like plumbing, restoration, inspections, and construction to create a full-service solution. Dave also shares his long-term vision for taking ProTec national—and the systems, processes, and technology he’s investing in to scale efficiently. This episode also covers: Why preventive maintenance is the “holy grail” for HOAs The importance of coaching, mentorship, and peer learning in entrepreneurship What it takes to build a great management team and step out of daily firefighting Dave’s passion for skiing, the power of de-stressing, and staying creative as a founder How insurance and deferred maintenance are creating major risk in HOA communities nationwide Whether you’re scaling a service-based business, thinking about M&A, or curious about building something meaningful in a niche industry, this episode is packed with wisdom from a founder who’s in it for the long haul. Links: ProTec Building Services: Dave on LinkedIn - Seth on LinkedIn - Topics: (00:00:00) - Intro (00:02:18) - Meet Dave (00:04:00) - Understanding ProTec's Business Model (00:05:54) - Challenges and Opportunities in HOA Maintenance (00:07:27) - The Importance of Preventive Maintenance (00:11:31) - Navigating HOA Insurance and Legal Issues (00:19:42) - The Founder’s Journey: From City Planning to ProTech (00:21:45) - Financing the Business and Early Challenges (00:22:17) - The Importance of Coaching and Mentorship (00:22:44) - Advice for Aspiring Entrepreneurs (00:28:32) - Building a Strong Management Team (00:32:46) - Balancing Work and Personal Passions (00:37:07) - Future Vision and Industry Trends (00:42:03) - Closing Remarks and Final Thoughts /episode/index/show/8b573379-d184-42ce-88fc-90115eccbbeb/id/35844485

Operational Agility: Pioneering Private Equity through Human Capital - Matt Schachman - Co-Founder - Cold Bore Capital 02/20/2025

Building a Billion Dollar Business in 3 Years - Steve Carroll - CEO of Kelso Industries 01/16/2025

Serial Entrepreneurship and What it Means to Take Ownership of a Business - Matt Matros - Founder and GP at NCC 12/19/2024

Frank Campise - Co-Founder and Principal of Jab Real Estate 11/21/2024

Navigating Growth and Private Equity: Reid Lappin and Henry Byrne on Scaling Vokal in the Digital Age 10/17/2024

Building a Restoration Empire: Chris Santiago on Scaling, Operations, and Culture in the Lower Mid-Market 09/26/2024

Welcome to Diners and Deals 09/11/2024

Diners and Deals

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